Piperidine → Phenylmethyl alpha-[[[2-(diethylamino)ethyl]thio]methyl]benzenepropanoate

HRID 36749

Reaktionsgleichung

Reaktionsgleichung von HRID 36749
[CH2:1]=[C:2]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].Cl.[CH2:21]([N:23]([CH2:27][CH3:28])[CH2:24][CH2:25][SH:26])[CH3:22].N1CCCCC1.[OH-].C([N+](C)(C)C)C1C=CC=CC=1>CO>[CH2:21]([N:23]([CH2:27][CH3:28])[CH2:24][CH2:25][S:26][CH2:1][CH:2]([CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:3]([O:5][CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)=[O:4])[CH3:22]

Komponenten

6

Edukt 4

HCID 8082PiperidineHCID 16031Ethanethiol, 2-(diethylamino)-, hydrochloride (1:1)HCID 66854Benzyltrimethylammonium hydroxideHCID 10912012Benzyl 2-Benzylacrylate

Produkt 1

HCID 19937709Phenylmethyl alpha-[[[2-(diethylamino)ethyl]thio]methyl]benzenepropanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

The oil prepared in Step 10 (1.5 g, 5.95 mmol) is dissolved under argon in methanol (22 mL). To this solution is added 2-diethylaminoethanethiol hydrochloride (1 g, 5.95 mmol), piperidine (0.78 mL, 7.85 mmol) and benzyltrimethylammonium hydroxide (0.25 mL, 0.6 mmol), and the mixture is stirred at room temperature for 16 hours. The solvent is removed on a rotary evaporator and then the residue is purified by flash chromotography on silica gel to give the pure title compound.

Aufarbeitung

  1. customThe solvent is removed on a rotary evaporator
  2. customthe residue is purified by flash chromotography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-f0be70e54984436190edaae29acd41ab
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05416119

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